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When Jenny Dumped Benny

The entertainment industry is rife with stories about entertainers fighting with the people they hire to serve them. In 1999, Madonna ended a bitter feud with her manager, Freddy DeMann, by forcing him out of the record label they started. Last year, George Clooney fired his talent agent, who had demanded a real estate finder's fee from the person who sold Mr. Clooney a villa at Lake Como, Italy.

But while tiffs like these are as common as liposuction and chai lattes here, Hollywood has seen nothing in recent memory like the breakup of Jennifer Lopez and her longtime manager, Benny Medina, the man who helped turn ''Jenny from the block'' into a household brand. After firing him in June, Ms. Lopez took the unusual step of filing a complaint with California's labor commission against Mr. Medina, saying he illegally contracted work on her behalf and misappropriated more than $100,000.

Mr. Medina has denied the accusations and both camps say they are close to settling their differences. An agreement could be announced this week. But it has been such a damaging battle from a publicity standpoint -- the New York tabloids have carried a running account -- that Ben Affleck, whom Ms. Lopez plans to marry this year, stepped in to help broker a resolution. The couple could ill-afford to have the fight overshadow the July 30 release of the film ''Gigli,'' in which they star.

The Jenny-Benny dispute has highlighted the fine lines in Hollywood that separate the roles of personal manager, producer, fashion executive and confidant. In the handling of veritable entertainment conglomerates like Ms. Lopez, whom associates say may have earned as much as $60 million last year from her acting, singing and fashion ventures, those lines have become increasingly blurred. With so much money at stake -- and the potential payout to advisers and handlers ever more lucrative -- some stars are more intent than ever on retaining control of their careers. That includes Mr. Affleck, who associates say has had a big influence on Ms. Lopez's recent decisions to keep tighter personal rein on her business affairs than had been her habit under Mr. Medina -- whom in the past was as much her friend as her manager.

''In the entertainment world there are two kinds of divas -- the kind that doesn't pay attention to the details and the one who counts the silverware,'' said Martin Kaplan, the director of the Norman Lear Center at the University of Southern California. ''In the end, friendship should have nothing to do with money, accountability and credibility.''

Both Ms. Lopez and Mr. Medina declined to comment on their business breakup or the nature of their relationship before and after. But several people who have worked with both Mr. Medina and Ms. Lopez say the two were virtually inseparable soon after he became her personal manager five years ago, having been introduced by the hip-hop singer and producer Sean Combs, known lately as P. Diddy, who was then a Medina client and was dating Ms. Lopez.

Mr. Medina, whose life inspired the sitcom ''Fresh Prince of Bel Air'' and who founded Handprint Entertainment, has had a client list that included Mr. Combs, the actor Will Smith and the singer Babyface. But it was managing Ms. Lopez for which he became best known.

At Ms. Lopez's wedding in 2001 to her second husband, Cris Judd, Mr. Medina was not only the best man, but joined the couple on their honeymoon. When Ms. Lopez and Mr. Medina traveled on business, they stayed in adjoining hotel suites. And many of the other people advising Ms. Lopez were handpicked by Mr. Medina.

''There was no perception she did not have that wasn't fed into by him,'' said one longtime colleague of the two, who compared the relationship to a platonic marriage.

By all accounts Mr. Medina was a tireless promoter -- one who was paid handsomely. Some industry executives estimate his annual take from his work for Ms. Lopez at $6 million. He received 10 percent of Ms. Lopez's earnings in film and television, according to the filed complaint, 15 percent of music publishing and recording and 10 percent of ancillary businesses, including the J. Lo clothes line and Glow perfume. In addition, Mr. Medina was to receive 50 percent of the producing revenue generated by Ms. Lopez's new production company, Nuyorican Productions.

And he enjoyed many of the diva-worthy perks afforded his star client, friends say. When Ms. Lopez was offered cosmetics and gifts from L'Oréal for doing advertisements, colleagues say Mr. Medina got them, too. He flew first class, on a movie studio's or record company's tab. Like Ms. Lopez, he had homes in both Los Angeles and New York. Several people who know Mr. Medina said calls placed to Ms. Lopez were returned only by him -- even if at times he would put the caller on hold while he conducted other clients' business.

And by all accounts, for most of their five years together, Ms. Lopez went along with the arrangement, protected by an army of managers, stylists and handlers. Although Ms. Lopez was involved in every decision, both camps say, they were largely filtered by Mr. Medina. ''She could have picked up the phone, and called people but she chose not to,'' said one person who had worked for Ms. Lopez.

Last year, though, came signs that the relationship was beginning to fray. In August, the verbal management agreement the two had relied on from 1998 and 2002 was formalized in a contract. The intent, according to her lawyer, Barry L. Hirsch, was to establish in writing that Mr. Medina would work solely for Ms. Lopez.

And Mr. Affleck, Ms. Lopez's new beau, had additional suggestions. He pointed out that her business manager, Ken Starr, did not have a cap on his salary, according to two people who talked to Ms. Lopez. (A business manager, who manages the finances, is separate from a personal manager, like Mr. Medina, who helps shape a career.)

Mr. Affleck thought she was paying Mr. Starr too much and, despite protests from Mr. Medina, according to the two people, she switched to Mr. Affleck's business manager, Murphy & Kress. And Mr. Affleck, who friends say tries to keep a low profile despite his star status, was said to be alarmed that Ms. Lopez was a frequent subject of tabloid reports, something her management team had a hard time containing. ''In Jennifer's mind it was normal,'' said a studio executive who has worked with both Mr. Affleck and Ms. Lopez. ''It was not, in Ben's.''

Mr. Affleck declined to discuss his relationship with Ms. Lopez. But according to one person who knows them both, ''Ben came in and said, 'I run a tighter ship.' ''

Problems erupted in October when Ed Limato, an agent at International Creative Management who had only recently begun representing Ms. Lopez, wrote a letter to Mr. Medina (with a copy to Ms. Lopez) saying he did not want to work for her. One frustration for Mr. Limato, who guided the careers of Denzel Washington and Mel Gibson, was that he and Ms. Lopez never talked -- that all dealings were through Mr. Medina.

''I'm not very good at dealing with phantom clients,'' he wrote in the letter, which was widely distributed in Hollywood at the time, ''as my greatest relationships and successes have been with artists with whom I have daily communications and enjoy their full confidence.''

Within weeks, Ms. Lopez signed with Patrick Whitesell, an agent at the Endeavor Talent Agency who happened not only to be Mr. Affleck's agent, but his good friend, too. But while Ms. Lopez was now returning her own calls, said two people apprised of the relationship, Mr. Medina clashed with Mr. Whitesell. Mr. Whitesell declined to comment on his relationship with Mr. Medina. But according to these people, Mr. Medina had wanted Ms. Lopez to sign with a competitor, the Creative Artists Agency, which continued to actively pursue her at Mr. Medina's urging. Mr. Whitesell, for his part, thought Mr. Medina was in over his head, the people said.

Ms. Lopez seemed to be, too, for that matter. The movie director Adam Shankman sued Ms. Lopez in May, saying she had stolen his idea for a movie on the opera ''Carmen,'' which she wanted to produce with Mr. Medina. And while her perfume Glow was a big seller, Ms. Lopez saw little of the profit herself because of the way her business deal was structured, according to one person apprised of the deal.

With her new set of advisers and a business-savvy boyfriend who was pushing her to shore up her finances, Ms. Lopez began to question why she was not making more money. So in late spring a host of accountants combed through her financial records, said three people briefed on the review, and questioned, among other things, payments of more than $100,000 to Mr. Medina. The complaint filed earlier this month described the amount as a misappropriated ''consulting fee.''

''The new accountants came in and said, 'What's this?' '' one of the people said. He said that Mr. Medina explained the payments as being reimbursements for expenses for which he did not save receipts.

By early June the relationship with Mr. Whitesell and Mr. Medina was so contentious, according to the two camps, that Mr. Whitesell gave Ms. Lopez a choice: him or Mr. Medina. She chose neither, firing Mr. Whitesell first and then Mr. Medina a few days later. (She fired her publicist, too.) Within days she had a new agent, her third in less than a year, and a new personal management company, too: The Firm.

One person who had worked with Mr. Medina and Ms. Lopez from the beginning wondered aloud whether the split had anything to do with the fact that, for the first time in five years, Mr. Medina had not been on the set, while Ms. Lopez was making the movie ''An Unfinished Life'' in Canada this past spring. ''With the extended separation,'' this person said, ''the relationship came under scrutiny.''

But he acknowledged that the reasons were probably more complicated. ''It was a mutual obsessiveness,'' this person said. ''You can't be in each others things in an intense way and not have it end some time.'' Still, he added, ''don't be surprised if Benny shows up at the wedding.''